US11083199B2ActiveUtilityPatentIndex 52
Heterocycle derivatives as pesticides
Est. expiryJan 10, 2037(~10.5 yrs left)· nominal 20-yr term from priority
Inventors:WILCKE DAVIDHAGER DOMINIKHOFFMEISTER LAURAKAUSCH-BUSIES NINAMOSRIN MARCWILLOT MATTHIEUFISCHER RUEDIGERILG KERSTINGOERGENS ULRICHTURBERG ANDREAS
C07D 471/04A01N 43/90C07D 403/04C07D 401/04C07D 487/04A01N 43/56A01N 43/50
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Claims
Abstract
The invention relates to novel compounds of the formula (I), in which X, R 1 , R 2 , R 3 , and n have the meanings given above, to the use thereof as acaricides and/or insecticides for controlling animal pests and to methods and intermediates for the preparation thereof.
Claims
exact text as granted — not AI-modifiedThe invention claimed is:
1. A compound of formula (I)
in which:
R 1 is (C 1 -C 6 )alkyl, (C 1 -C 6 )cyanoalkyl, (C 1 -C 6 )hydroxyalkyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )haloalkenyl, (C 2 -C 6 )alkynyl, (C 2 -C 6 )haloalkynyl or (C 3 -C 8 )cycloalkyl,
R 2 is hydrogen, (C 1 -C 6 )alkyl, (C 1-C 6 )haloalkyl, (C 1 -C 6 )cyanoalkyl, (C 1 -C 6 )hydroxyalkyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkoxy-(C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl,
R 3 is hydrogen, halogen, cyano, nitro, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkoxy, (C 1 -C 6 )alkylthio, (C 1 -C 6 )haloalkylthio, (C 1 -C 6 )alkylsulfinyl, (C 1 -C 6 )haloalkylsulfinyl, (C 1 -C 6 )alkylsulfonyl, (C 1 -C 6 )haloalkylsulfonyl, SCN, (C 1 -C 6 )alkylcarbonyl, (C 1 -C 6 )haloalkylcarbonyl, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )haloalkoxycarbonyl, aminocarbonyl, (C 1 -C 6 )alkylaminocarbonyl, di(C 1 -C 6 )alkylaminocarbonyl, (C 1 -C 6 )haloalkylaminocarbonyl, (C 3 -C 8 )cycloalkylaminocarbonyl, aminothiocarbonyl, (C 1 -C 6 )alkylaminothiocarbonyl, di(C 1 -C 6 )alkylaminothiocarbonyl, (C 1 -C 6 )haloalkylaminothiocarbonyl, (C 3 -C 8 )cycloalkylaminothiocarbonyl, amino, (C 1 -C 6 )alkylamino, (C 1 -C 6 )haloalkylamino, di(C 1 -C 6 )alkylamino, (C 3 -C 8 )cycloalkylamino, (C 1 -C 6 )alkylsulfonylamino, (C 1 -C 6 )alkylcarbonylamino, (C 1 -C 6 )haloalkylcarbonylamino, (C 1 -C 6 )alkylcarbonyl-(C 1 -C 6 )alkylamino, (C 1 -C 6 )haloalkylcarbonyl-(C 1 -C 6 )alkylamino, (C 3 -C 8 )cycloalkylcarbonylamino, (C 3 -C 8 )cycloalkylcarbonyl-(C 1 -C 6 )alkylamino, (C 1 -C 6 )alkylthiocarbonylamino, (C 1 -C 6 )haloalkylthiocarbonylamino, (C 1 -C 6 )alkylthiocarbonyl-(C 1 -C 6 )alkylamino, (C 1 -C 6 )haloalkylthiocarbonyl-(C 1 -C 6 )alkylamino, (C 3 -C 8 )cycloalkylthiocarbonylamino, (C 3 -C 8 )cycloalkylthiocarbonyl-(C 1 -C 6 )alkylamino, (C 2 -C 6 )alkenyl, (C 2 -C 6 )haloalkenyl, (C 2 -C 6 )cyanoalkenyl, (C 3 -C 8 )cycloalkyl-(C 2 )alkenyl, (C 2 -C 6 )alkynyl, (C 2 -C 6 )haloalkynyl, (C 3 -C 6 )cycloalkyl-(C 2 )alkynyl, (C 3 -C 6 )cycloalkyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylaminocarbonylamino, di(C 1 -C 6 )alkylaminocarbonylamino, (C 3 -C 6 )cycloalkylaminocarbonylamino, (C 1 -C 6 )haloalkylaminocarbonylamino, (C 1 -C 6 )alkylaminocarbonyl-(C 1 -C 6 )alkylamino, di(C 1 -C 6 )alkylaminocarbonyl-(C 1 -C 6 )alkylamino, (C 3 -C 6 )cycloalkylaminocarbonyl-(C 1 -C 6 )alkylamino or (C 1 -C 6 )haloalkylaminocarbonyl-(C 1 -C 6 )alkylamino,
or is aryl, hetaryl, cyclopentenyl or cyclohexenyl, each of which is optionally mono- or polysubstituted by identical or different substituents, wherein if R 3 is hetaryl at least one carbonyl group may optionally be present, and where optional substituents are as follows: cyano, carboxyl, halogen, nitro, acetyl, hydroxyl, amino, SCN, SF 5 , tri(C 1 -C 6 )alkylsilyl, (C 3 -C 8 )cycloalkyl, (C 3 -C 8 )cycloalkyl-(C 3 -C 8 )cycloalkyl, (C 1 -C 6 )alkyl-(C 3 -C 8 )cycloalkyl, (C 1 -C 6 )haloalkyl-(C 3 -C 8 )cycloalkyl, halo(C 3 -C 8 )cycloalkyl, cyano(C 3 -C 8 )cycloalkyl, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )cyanoalkyl, (C 1 -C 6 )hydroxyalkyl, hydroxycarbonyl-(C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )haloalkenyl, (C 2 -C 6 )cyanoalkenyl, (C 3 -C 8 )cycloalkyl-(C 2 )alkenyl, (C 2 -C 6 )alkynyl, (C 2 -C 6 )haloalkynyl, (C 2 -C 6 )cyanoalkynyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkoxy, (C 1 -C 6 )cyanoalkoxy, (C 1 -C 6 )alkoxycarbonyl-(C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxyimino, (C 1 -C 6 )haloalkoxyimino, (C 1 -C 6 )alkylthio, (C 1 -C 6 )haloalkylthio, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkylthio, (C 1 -C 6 )alkylthio-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulfinyl, (C 1 -C 6 )haloalkylsulfinyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkylsulfinyl, (C 1 -C 6 )alkylsulfinyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulfonyl, (C 1 -C 6 )haloalkylsulfonyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkylsulfonyl, (C 1 -C 6 )alkylsulfonyl-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylsulfonyloxy, (C 1 -C 6 )haloalkylsulfonyloxy, (C 1 -C 6 )alkylcarbonyl, (C 1 -C 6 )haloalkylcarbonyl, (C 1 -C 6 )alkylcarbonyloxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )haloalkoxycarbonyl, aminocarbonyl, (C 1 -C 6 )alkylaminocarbonyl, di(C 1 -C 6 )alkylaminocarbonyl, (C 1 -C 6 )haloalkylaminocarbonyl, (C 2 -C 6 )alkenylaminocarbonyl, di(C 2 -C 6 )alkenylaminocarbonyl, (C 3 -C 8 )cycloalkylaminocarbonyl, (C 1 -C 6 )alkylsulfonylamino, (C 1 -C 6 )alkylamino, di(C 1 -C 6 )alkylamino, (C 1 -C 6 )haloalkylamino, (C 3 -C 8 )cycloalkylamino, aminosulfonyl, (C 1 -C 6 )alkylaminosulfonyl, di(C 1 -C 6 )alkylaminosulfonyl, (C 1 -C 6 )alkylsulfoximino, aminothiocarbonyl, (C 1 -C 6 )alkylaminothiocarbonyl, di(C 1 -C 6 )alkylaminothiocarbonyl, (C 1 -C 6 )haloalkylaminothiocarbonyl, (C 3 -C 8 )cycloalkylaminothiocarbonyl, (C 1 -C 6 )alkylcarbonylamino, (C 1 -C 6 )haloalkylcarbonylamino, (C 1 -C 6 )alkylcarbonyl-(C 1 -C 6 )alkylamino, (C 1 -C 6 )haloalkylcarbonyl-(C 1 -C 6 )alkylamino, (C 3 -C 8 )cycloalkylcarbonylamino, (C 3 -C 8 )cycloalkylcarbonyl-(C 1 -C 6 )alkylamino, (C 1 -C 6 )alkylthiocarbonylamino, (C 1 -C 6 )haloalkylthiocarbonylamino, (C 1 -C 6 )alkylthiocarbonyl-(C 1 -C 6 )alkylamino, (C 1 -C 6 )haloalkylthiocarbonyl-(C 1 -C 6 )alkylamino, (C 3 -C 8 )cycloalkylthiocarbonylamino, (C 3 -C 8 )cycloalkylthiocarbonyl-(C 1 -C 6 )alkylamino, hetaryl, oxohetaryl, halohetaryl, halooxohetaryl, cyanohetaryl, cyanooxohetaryl, (C 1 -C 6 )haloalkylhetaryl or (C 1 -C 6 )haloalkyloxohetaryl,
X is a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the group of Q1 to Q12
R 4 is hydrogen, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )cyanoalkyl, (C 1 -C 6 )hydroxyalkyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, or (C 2 -C 6 )alkynyl,
R 5 is hydrogen, (C 1 -C 6 )alkyl, or (C 1 -C 6 )haloalkyl,
R 6 is hydrogen, and
n is 0, 1 or 2.
2. A compound of formula (I) according to claim 1 , in which
R 1 is (C 1 -C 4 )alkyl, (C 1 -C 4 )cyanoalkyl, (C 1 -C 4 )alkoxy-(C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 2 -C 4 )alkenyl, or (C 2 -C 4 )alkynyl,
R 2 is hydrogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )cyanoalkyl, (C 1 -C 4 )hydroxyalkyl, (C 1 -C 4 )alkoxy-(C 1 -C 4 )alkyl, or (C 1 -C 4 )haloalkoxy-(C 1 -C 4 )alkyl,
R 3 is hydrogen, halogen, cyano, nitro, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, (C 1 -C 4 )alkylsulfinyl, (C 1 -C 4 )haloalkylsulfinyl, (C 1 -C 4 )alkylsulfonyl, (C 1 -C 4 )haloalkylsulfonyl, SCN, (C 1 -C 4 )alkylcarbonyl, (C 1 -C 4 )haloalkylcarbonyl, (C 1 -C 4 )alkoxycarbonyl, (C 1 -C 4 )haloalkoxycarbonyl, aminocarbonyl, (C 1 -C 4 )alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, (C 1 -C 4 )haloalkylaminocarbonyl, (C 3 -C 6 )cycloalkylaminocarbonyl, aminothiocarbonyl, (C 1 -C 4 )alkylaminothiocarbonyl, di(C 1 -C 4 )alkylaminothiocarbonyl, (C 1 -C 4 )haloalkylaminothiocarbonyl, (C 3 -C 6 )cycloalkylaminothiocarbonyl, amino, (C 1 -C 4 )alkylamino, (C 1 -C 4 )haloalkylamino, di(C 1 -C 4 )alkylamino, (C 3 -C 6 )cycloalkylamino, (C 1 -C 4 )alkylsulfonylamino, (C 1 -C 4 )alkylcarbonylamino, (C 1 -C 4 )haloalkylcarbonylamino, (C 1 -C 4 )alkylcarbonyl-(C 1 -C 4 )alkylamino, (C 1 -C 4 )haloalkylcarbonyl-(C 1 -C 4 )alkylamino, (C 3 -C 6 )cycloalkylcarbonylamino, (C 3 -C 6 )cycloalkylcarbonyl-(C 1 -C 4 )alkylamino, (C 1 -C 4 )alkylthiocarbonylamino, (C 1 -C 4 )haloalkylthiocarbonylamino, (C 1 -C 4 )alkylthiocarbonyl-(C 1 -C 4 )alkylamino, (C 1 -C 4 )haloalkylthiocarbonyl-(C 1 -C 4 )alkylamino, (C 3 -C 6 )cycloalkylthiocarbonylamino, (C 3 -C 6 )cycloalkylthiocarbonyl-(C 1 -C 4 )alkylamino, (C 2 -C 4 )alkenyl, (C 2 -C 4 )haloalkenyl, (C 2 -C 4 )cyanoalkenyl, (C 3 -C 6 )cycloalkyl-(C 2 )alkenyl, (C 2 -C 4 )alkynyl, (C 2 -C 4 )haloalkynyl, (C 3 -C 6 )cycloalkyl-(C 2 )alkynyl, (C 3 -C 6 )cycloalkyl-(C 1 -C 4 )alkyl, (C 1 -C 4 )alkylaminocarbonylamino, di(C 1 -C 4 )alkylaminocarbonylamino, (C 3 -C 6 )cycloalkylaminocarbonylamino, (C 1 -C 4 )haloalkylaminocarbonylamino, (C 1 -C 4 )alkylaminocarbonyl-(C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylaminocarbonyl-(C 1 -C 4 )alkylamino, (C 3 -C 6 )cycloalkylaminocarbonyl-(C 1 -C 4 )alkylamino or (C 1 -C 4 )haloalkylaminocarbonyl-(C 1 -C 4 )alkylamino,
or is aryl, hetaryl, cyclopentenyl or cyclohexenyl, each of which is optionally mono- or polysubstituted by identical or different substituents, where if R 3 is hetaryl at least one carbonyl group may optionally be present, and where optional substituents are as follows: cyano, carboxyl, halogen, nitro, acetyl, hydroxyl, amino, SCN, SF 5 , tri(C 1 -C 4 )alkylsilyl, (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )cycloalkyl-(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkyl-(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )haloalkyl-(C 3 -C 6 )cycloalkyl, halo(C 3 -C 6 )cycloalkyl, cyano(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )cyanoalkyl, (C 1 -C 4 )hydroxyalkyl, hydroxycarbonyl-(C 1 -C 4 )alkoxy, (C 1 -C 4 )alkoxycarbonyl-(C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy-(C 1 -C 4 )alkyl, (C 2 -C 4 )alkenyl, (C 2 -C 4 )haloalkenyl, (C 2 -C 4 )cyanoalkenyl, (C 3 -C 6 )cycloalkyl-(C 2 )alkenyl, (C 2 -C 4 )alkynyl, (C 2 -C 4 )haloalkynyl, (C 2 -C 4 )cyanoalkynyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )cyanoalkoxy, (C 1 -C 4 )alkoxycarbonyl-(C 1 -C 4 )alkoxy, (C 1 -C 4 )alkoxy-(C 1 -C 4 )alkoxy, (C 1 -C 4 )alkoxyimino, (C 1 -C 4 )haloalkoxyimino, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, (C 1 -C 4 )alkoxy-(C 1 -C 4 )alkylthio, (C 1 -C 4 )alkylthio-(C 1 -C 4 )alkyl, (C 1 -C 4 )alkylsulfinyl, (C 1 -C 4 )haloalkylsulfinyl, (C 1 -C 4 )alkoxy-(C 1 -C 4 )alkylsulfinyl, (C 1 -C 4 )alkylsulfinyl-(C 1 -C 4 )alkyl, (C 1 -C 4 )alkylsulfonyl, (C 1 -C 4 )haloalkylsulfonyl, (C 1 -C 4 )alkoxy-(C 1 -C 4 )alkylsulfonyl, (C 1 -C 4 )alkylsulfonyl-(C 1 -C 4 )alkyl, (C 1 -C 4 )alkylsulfonyloxy, (C 1 -C 4 )haloalkylsulfonyloxy, (C 1 -C 4 )alkylcarbonyl, (C 1 -C 4 )haloalkylcarbonyl, (C 1 -C 4 )alkylcarbonyloxy, (C 1 -C 4 )alkoxycarbonyl, (C 1 -C 4 )haloalkoxycarbonyl, aminocarbonyl, (C 1 -C 4 )alkylaminocarbonyl, (C 1 -C 4 )haloalkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, (C 2 -C 4 )alkenylaminocarbonyl, di(C 2 -C 4 )alkenylaminocarbonyl, (C 3 -C 6 )cycloalkylaminocarbonyl, (C 1 -C 4 )alkylsulfonylamino, (C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, (C 1 -C 4 )haloalkylamino, (C 3 -C 6 )cycloalkylamino, aminosulfonyl, (C 1 -C 4 )alkylaminosulfonyl, di(C 1 -C 4 )alkylaminosulfonyl, (C 1 -C 4 )alkylsulfoximino, aminothiocarbonyl, (C 1 -C 4 )alkylaminothiocarbonyl, di(C 1 -C 4 )alkylaminothiocarbonyl, (C 1 -C 4 )haloalkylaminothiocarbonyl, (C 3 -C 6 )cycloalkylaminothiocarbonyl, (C 1 -C 4 )alkylcarbonylamino, (C 1 -C 4 )haloalkylcarbonylamino, (C 1 -C 4 )alkylcarbonyl-(C 1 -C 4 )alkylamino, (C 1 -C 4 )haloalkylcarbonyl-(C 1 -C 4 )alkylamino, (C 3 -C 6 )cycloalkylcarbonylamino, (C 3 -C 6 )cycloalkylcarbonyl-(C 1 -C 4 )alkylamino, (C 1 -C 4 )alkylthiocarbonylamino, (C 1 -C 4 )haloalkylthiocarbonylamino, (C 1 -C 4 )alkylthiocarbonyl-(C 1 -C 4 )alkylamino, (C 1 -C 4 )haloalkylthiocarbonyl-(C 1 -C 4 )alkylamino, (C 3 -C 6 )cycloalkylthiocarbonylamino, (C 3 -C 6 )cycloalkylthiocarbonyl-(C 1 -C 4 )alkylamino, hetaryl, oxohetaryl, halohetaryl, halooxohetaryl, cyanohetaryl, cyanooxohetaryl, (C 1 -C 4 )haloalkylhetaryl or (C 1 -C 4 )haloalkyloxohetaryl,
X is a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q1 to Q12,
R 4 is hydrogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )cyanoalkyl, (C 1 -C 4 )alkoxy-(C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkoxy-(C 1 -C 4 )alkyl, (C 2 -C 4 )alkenyl, or (C 2 -C 4 )alkynyl,
R 5 is hydrogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl,
R 6 is hydrogen, and
n is 0, 1 or 2.
3. A compound of formula (I) according to claim 1 , in which
R 1 is (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 2 -C 4 )alkenyl, (C 2 -C 4 )haloalkenyl or (C 3 -C 6 )cycloalkyl,
R 2 is hydrogen, (C 1 -C 4 )alkyl, or (C 1 -C 4 )haloalkyl,
R 3 is hydrogen, halogen, cyano, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, aminocarbonyl, (C 1 -C 4 )alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, (C 1 -C 4 )haloalkylaminocarbonyl, (C 3 -C 6 )cycloalkylaminocarbonyl, amino, (C 1 -C 4 )alkylamino, (C 1 -C 4 )haloalkylamino, di(C 1 -C 4 )alkylamino, (C 3 -C 6 )cycloalkylamino, (C 1 -C 4 )alkylsulfonylamino, (C 1 -C 4 )alkylcarbonylamino, (C 1 -C 4 )haloalkylcarbonylamino, (C 1 -C 4 )alkylcarbonyl-(C 1 -C 2 )alkylamino, (C 1 -C 4 )haloalkylcarbonyl-(C 1 -C 2 )alkylamino, (C 3 -C 6 )cycloalkylcarbonylamino, (C 3 -C 6 )cycloalkylcarbonyl-(C 1 -C 2 )alkylamino, (C 2 -C 4 )alkenyl, (C 2 -C 4 )haloalkenyl, (C 2 -C 4 )cyanoalkenyl, (C 3 -C 6 )cycloalkyl-(C 2 )alkenyl, (C 2 -C 4 )alkynyl, (C 3 -C 6 )cycloalkyl-(C 2 )alkynyl, (C 3 -C 6 )cycloalkyl-(C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxycarbonyl, aminothiocarbonyl, (C 1 -C 4 )alkylaminothiocarbonyl, di(C 1 -C 4 )alkylaminothiocarbonyl, (C 1 -C 4 )haloalkylaminothiocarbonyl,
or is phenyl, pyridyl, pyrimidyl, pyridazinyl, thiophenyl, furanyl, pyrazolyl, thiazolyl, oxazolyl, imidazolyl, pyrrolyl, cyclopentenyl or cyclohexenyl, each of which is optionally mono- or polysubstituted by identical or different substituents, where if R 3 is hetaryl at least one carbonyl group may optionally be present, and where optional substituents are as follows: cyano, halogen, (C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkyl-(C 3 -C 6 )cycloalkyl, halo(C 3 -C 6 )cycloalkyl, cyano(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )cyanoalkyl, (C 1 -C 4 )hydroxyalkyl, (C 1 -C 4 )alkoxy-(C 1 -C 2 )alkyl, (C 2 -C 4 )alkenyl, (C 2 -C 4 )haloalkenyl, (C 2 -C 4 )cyanoalkenyl, (C 3 -C 6 )cycloalkyl-(C 2 )alkenyl, (C 2 -C 4 )alkynyl, (C 2 -C 4 )haloalkynyl, (C 2 -C 4 )cyanoalkynyl, (C 1 -C 4 )alkylcarbonyl, (C 1 -C 4 )haloalkylcarbonyl, aminocarbonyl, (C 1 -C 4 )alkylaminocarbonyl, (C 1 -C 4 )haloalkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, (C 3 -C 6 )cycloalkylaminocarbonyl, aminothiocarbonyl, (C 1 -C 4 )alkylaminothiocarbonyl, di(C 1 -C 4 )alkylaminothiocarbonyl, (C 1 -C 4 )haloalkylaminothiocarbonyl, (C 3 -C 6 )cycloalkylaminothiocarbonyl, (C 1 -C 4 )alkylsulfonylamino, (C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, (C 1 -C 4 )haloalkylamino, (C 3 -C 6 )cycloalkylamino, aminosulfonyl, (C 1 -C 4 )alkylaminosulfonyl, di(C 1 -C 4 )alkylaminosulfonyl, (C 1 -C 4 )alkylcarbonylamino, (C 1 -C 4 )haloalkylcarbonylamino, (C 1 -C 4 )alkylcarbonyl-(C 1 -C 2 )alkylamino, (C 1 -C 2 )haloalkylcarbonyl-(C 1 -C 2 )alkylamino, (C 3 -C 6 )cycloalkylcarbonylamino, (C 3 -C 6 )cycloalkylcarbonyl-(C 1 -C 2 )alkylamino, (C 1 -C 4 )alkylthiocarbonylamino, (C 1 -C 4 )haloalkylthiocarbonylamino, (C 1 -C 4 )alkylthiocarbonyl-(C 1 -C 2 )alkylamino, (C 1 -C 4 )haloalkylthiocarbonyl-(C 1 -C 2 )alkylamino, (C 3 -C 6 )cycloalkylthiocarbonylamino or (C 3 -C 6 )cycloalkylthiocarbonyl-(C 1 -C 2 )alkylamino,
X is a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q1, Q2, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11 or Q12,
R 4 is hydrogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 2 -C 4 )alkenyl, or (C 2 -C 4 )alkynyl,
R 5 is (C 1 -C 4 )haloalkyl,
R 6 is hydrogen, and
n is 0, 1 or 2.
4. A compound of formula (I) according to claim 1 , in which
R 1 is methyl, ethyl, n-propyl, isopropyl, cyclopropyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,
R 2 is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,
R 3 is hydrogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 2 -C 4 )alkenyl, (C 2 -C 4 )haloalkenyl, (C 2 -C 4 )cyanoalkenyl, (C 3 -C 6 )cycloalkyl-(C 2 )alkenyl, halogen, cyano, (C 2 -C 4 )alkynyl, (C 3 -C 6 )cycloalkyl-(C 2 )alkynyl, (C 3 -C 6 )cycloalkyl-(C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxycarbonyl, aminocarbonyl, (C 1 -C 4 )alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, (C 1 -C 4 )haloalkylaminocarbonyl, aminothiocarbonyl, (C 1 -C 4 )alkylaminothiocarbonyl, di(C 1 -C 4 )alkylaminothiocarbonyl, (C 1 -C 4 )haloalkylaminothiocarbonyl,
or is phenyl, pyridyl, pyrimidyl, pyridazinyl, thiophenyl, thiazolyl, oxazolyl, imidazolyl, pyrazolyl, pyrrolyl, cyclopentenyl or cyclohexenyl, each of which is optionally mono- or polysubstituted by identical or different substituents—bridged via a carbon atom to the rest of the molecule—where optional substituents are as follows: cyano, halogen, nitro, acetyl, hydroxyl, amino, (C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkyl-(C 3 -C 6 )cycloalkyl, halo(C 3 -C 6 )cycloalkyl, cyano(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )cyanoalkyl, (C 1 -C 4 )hydroxyalkyl, (C 1 -C 4 )alkoxy-(C 1 -C 2 )alkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkoxy-(C 1 -C 2 )alkoxy, (C 1 -C 4 )alkoxyimino, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, (C 1 -C 4 )alkylsulfinyl, (C 1 -C 4 )haloalkylsulfinyl, (C 1 -C 4 )alkylsulfonyl, (C 1 -C 4 )haloalkylsulfonyl, (C 1 -C 4 )alkylcarbonyl, aminocarbonyl, (C 1 -C 4 )alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, (C 1 -C 4 )haloalkylaminocarbonyl, (C 3 -C 6 )cycloalkylaminocarbonyl, (C 1 -C 4 )alkylsulfonylamino, (C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, (C 1 -C 4 )haloalkylamino, (C 3 -C 6 )cycloalkylamino, (C 1 -C 4 )alkylcarbonylamino, (C 1 -C 4 )haloalkylcarbonylamino, (C 1 -C 4 )alkylcarbonyl-(C 1 -C 2 )alkylamino, (C 1 -C 4 )haloalkylcarbonyl-(C 1 -C 2 )alkylamino, (C 3 -C 6 )cycloalkylcarbonylamino, (C 3 -C 6 )cycloalkylcarbonyl-(C 1 -C 2 )alkylamino,
or is pyrazolyl or imidazolyl, each of which is optionally mono- or polysubstituted by identical or different substituents—bridged via a nitrogen atom to the rest of the molecule—where optional substituents are as follows: cyano, halogen, nitro, hydroxyl, amino, (C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, aminocarbonyl,
X is Q1, Q4, Q5, Q7, Q8, Q9, Q11 or Q12,
R 4 is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxymethyl or methoxyethyl,
R 5 is fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl, or pentafluoroethyl,
R 6 is hydrogen, and
n is 0, 1 or 2.
5. A compound of formula (I) according to claim 1 , in which
R 1 is ethyl or isopropyl,
R 2 is methyl, ethyl or isopropyl,
R 3 is hydrogen, bromine, cyano, ethenyl, cyclopropylethenyl, isopropenyl, cyclopropylethynyl, methyl, ethyl, isopropyl, cyclopropylethyl, methoxycarbonyl, trifluoroethylaminocarbonyl, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, ethylaminocarbonyl, aminothiocarbonyl, methylaminothiocarbonyl, dimethylaminothiocarbonyl,
or is phenyl, pyridyl, pyrimidyl, pyridazinyl, thiophenyl (thienyl), thiazolyl, imidazolyl, pyrazolyl, pyrrolyl or cyclohexenyl, each of which is optionally mono-, di- or trisubstituted by identical or different substituents—bridged via a carbon atom to the rest of the molecule—where optional substituents are as follows: cyano, fluorine, chlorine, methyl, cyclopropyl, cyanomethyl, cyanoisopropyl, cyanocylopropyl, trifluoromethyl, trifluoroethyl, aminocarbonyl,
or is pyrazolyl or imidazolyl, each of which is optionally monosubstituted by chlorine—bridged via a nitrogen atom to the rest of the molecule,
X is Q1, Q7, Q8, Q9 or Q12,
R 4 is methyl,
R 5 is trifluoromethyl,
R 6 is hydrogen, and
n is 0 or 2.
6. A compound of formula (I) according to claim 1 , having the structures according to Examples I-001 to I-098.
7. An agrochemical formulation comprising a compound of formula (I) according to claim 1 and one or more extenders and/or surfactants.
8. An agrochemical formulation according to claim 7 , additionally comprising a further agrochemical active ingredient.
9. Method for controlling one or more animal pests, comprising allowing a compound of formula (I) according to claim 1 or an agrochemical formulation thereof to act on the animal pests and/or a habitat thereof.
10. A product comprising a compound of formula (I) according to claim 1 or of agrochemical formulation thereof for controlling one or more animal pests.
11. The compound of formula (I) according to claim 5 , wherein X is Q1.
12. The compound of formula (I) according to claim 5 , wherein X is Q7.
13. The compound of formula (I) according to claim 5 , wherein X is Q8.
14. The compound of formula (I) according to claim 5 , wherein X is Q9.
15. The compound of formula (I) according to claim 5 , wherein X is Q12.Cited by (0)
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